2.0 2012-05-31 14:19:12 -0600 2015-12-09 12:08:06 -0700 ECMDB10616 M2MDB000798 PG(18:1(11Z)/16:1(9Z)) PG(18:1(11Z)/16:1(9Z)) is a phosphatidylglycerol. Phosphatidylglycerols consist of a glycerol 3-phosphate backbone esterified to either saturated or unsaturated fatty acids on carbons 1 and 2. As is the case with diacylglycerols, phosphatidylglycerols can have many different combinations of fatty acids of varying lengths and saturation attached to the C-1 and C-2 positions. PG(18:1(11Z)/16:1(9Z)), in particular, consists of one 11Z-octadecenoyl chain to the C-1 atom, and one 9Z-hexadecenoyl to the C-2 atom. In E. coli glycerophospholipid metabolism, phosphatidylglycerol is formed from phosphatidic acid (1,2-diacyl-sn-glycerol 3-phosphate) by a sequence of enzymatic reactions that proceeds via two intermediates, cytidine diphosphate diacylglycerol (CDP-diacylglycerol) and phosphatidylglycerophosphate (PGP, a phosphorylated phosphatidylglycerol). Phosphatidylglycerols, along with CDP-diacylglycerol, also serve as precursor molecules for the synthesis of cardiolipin, a phospholipid found in membranes. 1-(11Z-Octadecenoyl)-2-(9Z-hexadecenoyl)-sn-glycero-3-phospho-(1'-glycerol) 1-(11Z-octadecenoyl)-2-(9Z-hexadecenoyl)-sn-glycero-3-phosphoglycerol 1-phosphatidylglycerol 1-Vaccenoyl-2-palmitoleoyl-sn-glycero-3-phosphoglycerol 3(3-phosphatidyl-)glycerol 3-(3-<i>sn</i>-phosphatidyl)glycerol 3-(3-sn-Phosphatidyl)glycerol GPG(18:1/16:1) GPG(18:1n7/16:1n7) GPG(18:1w7/16:1w7) GPG(34:2) PG(18:1/16:1) PG(18:1n7/16:1n7) PG(18:1w7/16:1w7) PG(34:2) Phosphatidylglycerol Phosphatidylglycerol(18:1/16:1) Phosphatidylglycerol(18:1n7/16:1n7) Phosphatidylglycerol(18:1w7/16:1w7) Phosphatidylglycerol(34:2) C40H75O10P 746.9913 746.509785132 [(2S)-2,3-dihydroxypropoxy][(2R)-3-[(9Z)-hexadec-9-enoyloxy]-2-[(11Z)-octadec-11-enoyloxy]propoxy]phosphinic acid (2S)-2,3-dihydroxypropoxy(2R)-3-[(9Z)-hexadec-9-enoyloxy]-2-[(11Z)-octadec-11-enoyloxy]propoxyphosphinic acid [H][C@](O)(CO)COP(O)(=O)OC[C@@]([H])(COC(=O)CCCCCCC\C=C/CCCCCC)OC(=O)CCCCCCCCC\C=C/CCCCCC InChI=1S/C40H75O10P/c1-3-5-7-9-11-13-15-17-18-20-22-24-26-28-30-32-40(44)50-38(36-49-51(45,46)48-34-37(42)33-41)35-47-39(43)31-29-27-25-23-21-19-16-14-12-10-8-6-4-2/h13-16,37-38,41-42H,3-12,17-36H2,1-2H3,(H,45,46)/b15-13-,16-14-/t37-,38+/m0/s1 KSRFAXYFDXHNDB-GFJSAGKOSA-N Solid Inner membrane Membrane Outer membrane logp 8.01 ALOGPS logs -6.85 ALOGPS solubility 1.05e-04 g/l ALOGPS logp 11.1 ChemAxon pka_strongest_acidic 1.89 ChemAxon pka_strongest_basic -3 ChemAxon iupac [(2S)-2,3-dihydroxypropoxy][(2R)-3-[(9Z)-hexadec-9-enoyloxy]-2-[(11Z)-octadec-11-enoyloxy]propoxy]phosphinic acid ChemAxon average_mass 746.9913 ChemAxon mono_mass 746.509785132 ChemAxon smiles [H][C@](O)(CO)COP(O)(=O)OC[C@@]([H])(COC(=O)CCCCCCC\C=C/CCCCCC)OC(=O)CCCCCCCCC\C=C/CCCCCC ChemAxon formula C40H75O10P ChemAxon inchi InChI=1S/C40H75O10P/c1-3-5-7-9-11-13-15-17-18-20-22-24-26-28-30-32-40(44)50-38(36-49-51(45,46)48-34-37(42)33-41)35-47-39(43)31-29-27-25-23-21-19-16-14-12-10-8-6-4-2/h13-16,37-38,41-42H,3-12,17-36H2,1-2H3,(H,45,46)/b15-13-,16-14-/t37-,38+/m0/s1 ChemAxon inchikey KSRFAXYFDXHNDB-GFJSAGKOSA-N ChemAxon polar_surface_area 148.82 ChemAxon refractivity 206.74 ChemAxon polarizability 88.79 ChemAxon rotatable_bond_count 40 ChemAxon acceptor_count 6 ChemAxon donor_count 3 ChemAxon physiological_charge -1 ChemAxon formal_charge 0 ChemAxon Glycerophospholipid metabolism ec00564 phospholipid biosynthesis I PHOSLIPSYN-PWY Specdb::CMs 773782 Specdb::CMs 773783 Specdb::CMs 773784 Specdb::CMs 773785 Specdb::CMs 773786 Specdb::CMs 773787 Specdb::CMs 773788 Specdb::CMs 773789 Specdb::CMs 773790 Specdb::NmrOneD 297315 Specdb::NmrOneD 297316 Specdb::NmrOneD 297317 Specdb::NmrOneD 297318 Specdb::NmrOneD 297319 Specdb::NmrOneD 297320 Specdb::NmrOneD 297321 Specdb::NmrOneD 297322 Specdb::NmrOneD 297323 Specdb::NmrOneD 297324 Specdb::NmrOneD 297325 Specdb::NmrOneD 297326 Specdb::NmrOneD 297327 Specdb::NmrOneD 297328 Specdb::NmrOneD 297329 Specdb::NmrOneD 297330 Specdb::NmrOneD 297331 Specdb::NmrOneD 297332 Specdb::NmrOneD 297333 Specdb::NmrOneD 297334 Specdb::MsMs 27050 Specdb::MsMs 27051 Specdb::MsMs 27052 Specdb::MsMs 33608 Specdb::MsMs 33609 Specdb::MsMs 33610 Specdb::MsMs 2698062 Specdb::MsMs 2698063 Specdb::MsMs 2698064 HMDB10616 24768115 C00344 L-1-PHOSPHATIDYL-GLYCEROL Keseler, I. M., Collado-Vides, J., Santos-Zavaleta, A., Peralta-Gil, M., Gama-Castro, S., Muniz-Rascado, L., Bonavides-Martinez, C., Paley, S., Krummenacker, M., Altman, T., Kaipa, P., Spaulding, A., Pacheco, J., Latendresse, M., Fulcher, C., Sarker, M., Shearer, A. G., Mackie, A., Paulsen, I., Gunsalus, R. P., Karp, P. D. (2011). "EcoCyc: a comprehensive database of Escherichia coli biology." Nucleic Acids Res 39:D583-D590. 21097882 Kanehisa, M., Goto, S., Sato, Y., Furumichi, M., Tanabe, M. (2012). "KEGG for integration and interpretation of large-scale molecular data sets." Nucleic Acids Res 40:D109-D114. 22080510 Uniprot Consortium (2012). "Reorganizing the protein space at the Universal Protein Resource (UniProt)." Nucleic Acids Res 40:D71-D75. 22102590 Yurtsever D. (2007). Fatty acid methyl ester profiling of Enterococcus and Esherichia coli for microbial source tracking. M.sc. Thesis. Villanova University: U.S.A Phosphatidylglycerophosphatase B P0A924 PGPB_ECOLI pgpB http://ecmdb.ca/proteins/P0A924.xml Phosphatidylglycerophosphatase A P18200 PGPA_ECOLI pgpA http://ecmdb.ca/proteins/P18200.xml Protein crcA P37001 CRCA_ECOLI crcA http://ecmdb.ca/proteins/P37001.xml Cardiolipin synthase P0A6H8 CLS_ECOLI cls http://ecmdb.ca/proteins/P0A6H8.xml Putative cardiolipin synthase ybhO P0AA84 YBHO_ECOLI ybhO http://ecmdb.ca/proteins/P0AA84.xml Cardiolipin synthase C P75919 CLSC_ECOLI clsC http://ecmdb.ca/proteins/P75919.xml Probable phospholipid ABC transporter-binding protein mlaB P64602 MLAB_ECOLI mlaB http://ecmdb.ca/proteins/P64602.xml Probable phospholipid ABC transporter-binding protein mlaD P64604 MLAD_ECOLI mlaD http://ecmdb.ca/proteins/P64604.xml Probable phospholipid ABC transporter permease protein mlaE P64606 MLAE_ECOLI mlaE http://ecmdb.ca/proteins/P64606.xml PE(P-18:1(11Z)/16:1(9Z)) + PG(18:1(11Z)/16:1(9Z)) > Ethanolamine + a cardiolipin PW_R003214